REP. JASON CHAFFETZ (R), UTAH: As a former military officer, you simply cannot take money from Russia, Turkey, or anybody else. And it appears as if he did take that money. It was inappropriate. And there are repercussions for the violation of law.

(END VIDEO CLIP)

LEMON: Plus, Caitlyn Jenner, why she says this about President Trump.

(BEGIN VIDEO CLIP)

CAITLYN JENNER, ACTOR: I would love to go down and play golf with him and say why the hell did you do that?

(END VIDEO CLIP)

LEMON: We want to get right to the latest on the Russia investigation. First, CNN's justice correspondent Pamela Brown has that -- Pamela.

PAMELA BROWN, CNN JUSTICE CORRESPONDENT: Well Don, today a top house Republican said Michael Flynn likely broke the law after failing to disclose payments he received from foreign governments before becoming President Trump's national security advisor.

Now the revelation comes after leaders of the House oversight committee reviewed classified documents in a private briefing. Speaking of reporters on Capitol Hill today, they revealed they have seen no proof showing Flynn, a former top military intelligence official received permission from the Pentagon or the state department for the foreign government payments that he received from both Russia and Turkey. And they say that he didn't fully disclose the more than half a million dollars his firm was given for lobbying activities on behalf of Turkey when he applied to reinstate his security clearance or the $45,000 he received from Russia for an RTTV speaking engagement, money that Congressman Chaffetz said Flynn might have to pay back.

The Ranking democrat on the committee Congressman Cummings also said Flynn likely broke the law for admitting the foreign payment off his 2016 application for security clearance for the national security advisor post. That is a possible felony punishable with up to five years in jail.

Now, Flynn's attorney said in a statement to CNN, he did comply with the law on the Russia payment saying quote General Flynn briefed the Defense Intelligence Agency, a component agency of DOD extensively regarding the RT speaking event trip both before after the trip" -- Don.

LEMON: All right. Pamela Brown, thank you very much.

Now I want to bring in CNN's senior political analyst Mark Preston, national security analyst, Juliette Kayyem, military analyst Colonel Cedric Leighton and CNN political commentator and former congressman, Jack Kingston.

Welcome to the program, one and all.

Mark, it seems pretty clear that the White House is trying to disown this foreign national security, the former national security advisor, but it's not going to fly, is it?

MARK PRESTON, CNN POLITICS EXECUTIVE EDITOR: No. And we don't actually know how intertwined it is right now and that's what the investigation is for. But the fact of the matter is, they are very much in sneered because he held such a high profile role. And quite frankly, with the top secret clearance that he had and him not only misleading at least it appears what his speech was to RT and how much money he made and what have you or that's what we are led to believe from congressional investigators.

He also misled Mike Pence which eventually led to his dismissal from the White House. So the White House is in sneered in this. They are very tangled up. And it certainly is going to take a few months, you know, if not longer for this all to be untangled.

LEMON: Colonel Leighton, you know Michael Flynn, you served under him. What do you think about these new allegations that he may have broken the law?

MAJ. COL. CEDRIC LEIGHTON (RET.), CNN MILITARY ANALYST: Well, it's a huge disappointment, Don. And the real big thing here is that, you know, when you are in the military and especially when you are in the intelligence business, you have a lot of high standards to uphold. And when someone fails or is alleged to have failed to meet those standards, then you have a real problem. And it's from that standpoint that I'm very disappointed and I also think that there probably is a lot more information to come out on this.

LEMON: So, Colonel, he filled out the security clearance from about a form about a month after the trip to Moscow, where we saw him sitting with Vladimir Putin by the way, can you think of any reason why he wouldn't have disclosed that?

LEIGHTON: Not at all. In fact, any little thing, I remember, you know, when I filled out my forms, I had friends in different parts of the world. I made sure that the investigators knew exactly who those people were, what their addresses were. And what my relationship was with them. And it is not that hard to do. It's just good to be open about this stuff. And apparently General Flynn wasn't.

LEMON: Yes, Juliette, Flynn was paid $45,000 by RT. He sat with Vladimir Putin. He got $500,000 from a Turkish lobbying firm. Wouldn't the White House have turned up that in their vetting or no?

JULIETTE KAYYEM, CNN NATIONAL SECURITY ANALYST: Yes. I mean, by Google search. So the White House will claim likely that they don't do vetting outside of what DOD or whoever was holding his security clearance did, but these stories about Flynn's relationship with Russia in particular, but there is also Turkey, were appearing by mid- 2016. So it's not like, you know, when he becomes national security advisor a couple months later that there should have been a surprise about some of his affiliations. So the person doing the review let alone the White House counsel's office would have known and been aware of the omissions.

And just to pick up on what the colonel said, people outside the national security field should not believe that this is like onerous oversight, you know, that oh, he just forgot. This is part of our blood. In terms of who we are in the national security clearance process and disclosing every trip we make even if we go to Ireland with our family or we have a friend who works for a foreign government. This is part of, you know -- it's sort of no different than a doctor having to, you know, take an exam. This is who we are. So the idea that this was anything but clear intent by Mike Flynn. It just has to be more. He had been in the business for too long.

[23:06:13] LEMON: Yes. And omission, right, at the very least. It was an omission, but.

Jack, Representative Chaffetz and Cummings asked the White House for documentation related to Flynn and here is part of what the press secretary Sean Spicer said about it today.

(BEGIN VIDEO CLIP)

SEAN SPICER, WHITE HOUSE PRESS SECRETARY: And he asked for documents prior to January 28th. As you know through the constitution, we didn't assume the White House until January 20th, so we don't have the documents prior to assuming the White House. And then the third would be they listed for every call and contact that he made which is an extraordinary number that that's a very un-wielding request.

(END VIDEO CLIP)

LEMON: OK, so Jack, how can there be no record of Flynn's work during the transition? He was working on behalf of the government. And is the White House saying that the request is too big or they won't comply on other grounds?

Well, the White House actually has issued a statement that they do want to comply with the house request. Some of was too broad. I think the list of all those phone calls, for example, may be the transition committee still has that and maybe the White House does, but certainly that might take some time to put together.

Elijah Cummings, the lead democrat said that the White House is not acted in a way that's been obstructionist. But you know, one of the things that's curious is that General Flynn's own lawyer is saying before the Moscow trip he did disclose that to the defense or to the national intelligence -- I don't know if it was DIA or Nia or whatever the authority might be --

KAYYEM: DIA.

KINGSTON: And so, he say and he did disclose that, that would have been done of course under the Barack Obama administration, those records are out there somewhere. And I think we could find out quickly. Did he in fact disclose those or did he not?

LEMON: Colonel, do you want to say something?

LEIGHTON: Yes, Don, there are two things here. Yes, he did talk to DIA, apparently, and say that he had gone on the trip or was going to go on the trip. That's well and good. The problem is though that there are other things that he needed to do in order to make it completely legal. He needed to get clearance from not only the secretary of state, but also the secretary of the army in order to actually, legally get the money that he received from both Turkish source and Russian sources.

The fact that he didn't do that is I think what is troubling the congressional committee and I think that's also where he's in legal hot water. So he may have notified the DIA, but the failure to notify the other entities at very lie level, secretary of state and secretary of the army, that spells trouble for him.

LEMON: Mark, do you believe that the House is in compliance? That they want to comply with this? The White House?

PRESTON: No, no. I mean, I don't think so because I don't think they want to, as we said right at the top, I don't think they want to be anymore tied to his than they have to be. And I literally wrote down some of the reason why is they chose not to comply with it. Some of it is in the fact that they say that didn't have the records. But they do want to say that, you know, that they don't have documents because if pre-dates with the White House. But look, he was an advisor on the campaign. And if you are going to run a very tight ship so to speak then certainly to have somebody who is going to be helping oversea. You have national security in help lead that effort. You got to know what to do.

LEMON: General Flynn's attorney says that Flynn did brief the defense agency as Jack said extensively about his (INAUDIBLE) trip before and after. He also offered Flynn's testimony in exchange for immunity. I mean, what are the chances of that Mark Preston?

PRESTON: Who knows? I mean, again, that's what we will see when the investigation (INAUDIBLE) brought up an interesting point earlier saying that basically is not Congress's point to say whether they are guilty or innocent. They are there to investigate. It's up to the FBI where there's smoke, there's fire.

You know, I do think it is worth saying this and perhaps the colonel, you know, can attest to it. This is a tragedy. This is something who gave his whole life, his career, you know, really achieved, you know, a place in our history that very few do as general, and this is where he is right now.

[23:10:26] LEMON: Very rarefied position.

Colonel, I have to ask you another question, though. If it is found out that he concealed information about his trips and payments and to foreign -- from foreign governments and so forth. How much trouble is Michael Flynn in?

LEIGHTON: A lot of trouble, Don, a lot of trouble. And you know, it could point to all kinds of other things that, you know, are right now in the realm of speculation. But, you know, if I were the FBI, I would certainly be looking at not only the failure to report these things, but what actually happened during these trips and what other relationships general Flynn may have had with the Russians or any other foreign entities.

LEMON: Yes. We have to end it there. Thank you all very much. I appreciate it.

When we come back, Ivanka Trump in Berlin speaking on a panel with female business leaders. But facing a tough audience why she was booed and how she handled it.

And later, I speak to Caitlyn Jenner. Is she thinking about running for office?

Plus, I have a programming note for you, I want to give you a look at CNN original series, "Sound Tracks, Music That Defined History." This Thursday night at 10:00, a look at the songs that took on a whole new meaning in the wake of 9/11. Here's a preview.

(BEGIN VIDEO CLIP)

UNIDENTIFIED MALE: The music and the artist post-9/11, they are reflective of the many emotions we feel.

UNIDENTIFIED MALE: We played for an audience of police and firemen and emergency rescue workers. And they needed a boost.

UNIDENTIFIED MALE: I put a fireman's helmet on the piano just to help me concentrate. Just if I didn't have that, I might have just lost it.

UNIDENTIFIED MALE: It is kind of an anthem for New York City. I didn't think of that when I wrote it.

UNIDENTIFIED MALE: The events that transpired to find the music and made it bigger than it was intended to be.

UNIDENTIFIED MALE: Music will always remind us that it is possible.

UNIDENTIFIED MALE: Somebody's got to put this into words and emotions. That is what anthems are made of.

UNIDENTIFIED MALE: Sound tracks, songs that defined history Thursday at 10:00 on CNN.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

[23:16:05] LEMON: First daughter, Ivanka Trump was booed today after defending her father at a women's forum in Berlin.

(BEGIN VIDEO CLIP)

IVANKA TRUMP, PRESIDENT TRUMP'S DAUGHTER: She's been a tremendous champion of supporting families and -- the new reality of --

UNIDENTIFIED FEMALE: The reaction from the audience.

I. TRUMP: I certainly heard the criticism of the media and that's per pitch waited.

Good evening to all of you. And good morning to you, Emily, there in Berlin. Thank you so much for joining us. It is 5:00 a.m., so you're up early. You were there, you were surprised she got this type of reaction from the audience. Were you?

EMILY JANE FOX, STAFF WRITER, VANITY FAIR: Well, I think when you invite a person who is a member of the administration, she came at the request of Angela Merkel, and I think sitting in the audience, I was surprised to hear this reaction. I will have you know that just before she went on, we were reminded in the audience to twice before the queen of the Netherlands who was also on the panel to stand up to make sure that they showed her adequate respect. And so it caught me particularly by surprise that then there were these audible hisses and groans when Ivanka Trump was on stage defending her father.

LEMON: Emily, she has been a really tireless and fierce defender of her father. And she is in a very difficult position trying to square her father's record on women's issues with her own stance, right?

FOX: Yes. And I think what is lost here and what I think often happens with Ivanka Trump is that she had a very good day personally. She was great on stage. She was very on message. She was touting all of the things she had studied up on, all of the things she wants to do. She brought ideas for solutions to solve some of the problems facing women entrepreneurs. And unfortunately, the headline out of this is still she is being dragged down by the associations people have with her father.

And this was a great visit. A great first trip abroad for Ivanka Trump. And the headline to me is that she is still being dragged down with her connected to her father. Actually, as we speak, there are tons of police motorcycles driving right by she is staying at the hotel right here, and I think she is preparing to leave Berlin.

LEMON: Yes. And as that happens, I want to play another part of from Ivanka Trump speaking in Berlin. Watch.

(BEGIN VIDEO CLIP)

I. TRUMP: I think the thousands of women who worked with and for my father for decades when he was in the private sector are testament to his belief and solid conviction in the potential of women.

(END VIDEO CLIP)

LEMON: So Kayleigh, thousands of women, where is that number coming from?

KAYLEIGH MCENANY, CNN POLITICAL COMMENTATOR: Well, I mean, he has been running a business for decades now. I mean, he was known for empowering women in the construction industry back when no men was doing that back when it was, you know, politically unpalatable or just not common in the industry to have women in construction. He was doing that. So I think that number probably comes from decades of him having a business. And you know, I would also point, look at this campaign. You know, elevating Kellyanne Conway, the first successful female campaign manager. She is another woman who doesn't get notoriety she has for the lead of President Trump.

LEMON: Yes. There's a lot to say about that because there were several other people before her and she was sort of the last ditch effort to pull him back to pull the train back on the track.

But with that said, Richard, Ivanka also struggled when she was asked what exactly her role in the White House is. And she told the audience this. Watch.

(BEGIN VIDEO CLIP)

I. TRUMP: I am rather unfamiliar with this role as well as it is quite new to me. It has been a little under 100 days, but it is just been a remarkable, incredible journey. I am humbled to be here with so many formidable leaders to engage in dialogue, to learn, to bring the advice, to bring the knowledge back to the United States, back to both my father and the President. And hopefully that will bring about incremental positive change. And that is my goal.

(END VIDEO CLIP)

[23:20:29] LEMON: So Richard, it has been a month since Ivanka's official job was announced. Is her role still that unclear?

RICHARD PAINTER, CHIEF WHITE HOUSE ETHICS LAWYER UNDER GEORGE W. BUSH: Well, it is quite unclear. There are a number of things she can't do because of financial conflicts of interest. She can't get involved with trade negotiations (INAUDIBLE) over clothing imports because that's the business she's in. And she can't get involved in things that affect her husband's real estate business, such as the tax code, tax reform, and the banking regulations.

There are other things she can do, but it's not clear what she is doing in the White House. She may very well be a calming influence on her father and I think that could be very good in these difficult times. And she also perhaps can persuade him to ease out of the White House, some of the more extremist elements from the alt-right who have done damage to him politically. But it's unclear what she is doing right now. And she is going to have to figure that out with her father.

LEMON: Emily, you are there and you have been reporting on her, what is she actually doing? And the other question is, you know, you have said and others have said, well her beliefs are I divergent to her fathers. But maybe, I mean, isn't sort of guilt by association and maybe if her father is the President of the United States that sort of that's what she believes as well. And it's not going to change because getting boos is a sign of that.

FOX: Well, I think that you're right. Yesterday was a sign that it's very hard for her to wash the stain of her father off, regardless of what she is doing. And I think that anyone in the Trump White House is going to have difficulty separating themselves from their opinion about what the President is doing.

She was almost treated like a celebrity here though. We were following her in the motorcade and there were people along the streets, holding up their smart phones, waiting to see her pass. I went with her to the holocaust memorial here. And there were hundreds of people along the way, at the holocaust memorial just waiting to catch a glimpse of her on their smart phones.

So whether or not people understand what she is doing, they know who she is and they are very intrigued to see what she's going to do as part of the administration.

LEMON: Thank you, all. Our time is short. I apologize. Thank you so much. I appreciate it.

When we come back, President Trump failing to keep many of his campaign promises. But are his supporters regretting their votes?

Plus I'm going to speak to Caitlyn Jenner, does she regret voting for Trump? The answer is next.

(COMMERCIAL BREAK)

[23:26:53] LEMON: With almost 100 days behind him, President Trump is seeing the lowest approval ratings of any newly elected President in modern history. But among his voters, he has 94 percent support. Tonight they tell CNN they are happy with the President even if he is not fulfilling every campaign promise.

MARTIN SAVIDGE, CNN CORRESPONDENT (voice-over): Ashville, Alabama. The sun's been up for three hours and Greg Weston has been up for six. He is a form farmer. What he grows, he and his wife Brandy, sell in an old gas station on the edge of town.

GREG WESTON, FARMER: This is the western foreign.

SAVIDGE: Round here, the only thing redder than the matters is the politics. The county where Greg and Brandi lives voted 89 percent for Trump. How do you think Trump's doing?

G. WESTON: I think he is doing good.

SAVIDGE: They like Trump even though his first actions haven't really helped him. Trump's immigration talk made it harder for Greg to find migrant workers to harvest his crops.

G. WESTON: Can't get it picked, then you're in trouble.

SAVIDGE: Then there's Trump's efforts to replace Obamacare which Greg and Brandy are on.

Why do you like it?

G. WESTON: Well, I pay $88 a month for me and my wife. Where I was like -- before Obamacare come in, I was paying like 6.60.

SAVIDGE: Obamacare is working so well Brandy feels guilty. She says she knows people who can't afford their private insurance or can't get insurance at all. She's OK with Trump's efforts to replace it.

BRANDI WESTON, FARMER: It still doesn't make sense to pay so little and still the poor people get nothing.

SAVIDGE: You think you should pay more?

B. WESTON: Yes. In other word, yes.

SAVIDGE: In Birmingham, it's also another long day for Quinton Posey, cab driver. In the past, he has voted democratic, but in 2016, voted Trump.

QUINTON POSEY, TAXI DRIVER: The thing about a businessman is that it's action. And it's not policy.

SAVIDGE: Black Trump voters are rare in the south, only about nine percent. Quinton is even more rare since he is black and gay. 100 days in, how do you feel he's done?

POSEY: 100 days in, I'm not pleased.

SAVIDGE: Really?

POSEY: Not pleased.

SAVIDGE: What don't you like?

POSEY: He is a little too brash, is that the word?

SAVIDGE: Quinton hasn't seen as much change as he expected. And he worries about what a Trump budget might cut. I mean, did you wish you hadn't voted for him?

POSEY: I don't wish I had, I mean, according to the alternatives, I don't have any regrets.

SAVIDGE: Right. You were not going to vote for Clinton?

POSEY: No, not voting for her.

SAVIDGE: In Des Moines, Iowa, I find another surprise. Named Alberto Alejandre, the 32-year-old public school teacher who teaches Spanish to inner city kids. Who did you vote for?

ALBERTO ALEJANDRE, SCHOOL TEACHER: I voted for Trump.

SAVIDGE: Born in Mexico, he became an American through an amnesty program in the '80s, yet voted for a President who was called Mexican's criminals and threatens mass deportations.

[23:30:04] ALEJANDRE: Here we are 100 days after he was sworn in and he has not acted against innocent undocumented workers.

SAVIDGE: Some would disagree, but what's certain is that Alberto feels good about the administration so far, including on immigration.

ALEJANDRE: Being in America to begin with is a right, it's a great privilege.

SAVIDGE: Madison county, Iowa, famous for bridges and home to a many feel personifies America, Jon Wayne. Brian Downes knew the duke and found similar qualities in the Donald when he met Trump at a campaign event. Meeting him made a huge difference.

BRAIN DOWNES, TRUMP VOTER: Yes, made a huge difference. It's somebody who we really felt like one of us. I had that feeling.

SAVIDGE: The big campaign issue for Brian was the same as Alberto.

DOWNES: Borders. Immigration. And I think the national security is all part of that.

SAVIDGE: And like Alberto, Brian is pleased by Trump so far.

DOWNES: I think he's doing great.

SAVIDGE: And he also admits that Trump's had to deal with a bit of a learning curve.

DOWNES: And as much as admitted, I didn't know it was going to be this conflicted.

SAVIDGE: From the birthplace of Jon Wayne to a scene right out of the old west. John's family has been raising buffalo since the '60s. Today the (INAUDIBLE) ranch has more than 3,000.

UNIDENTIFIED MALE: They are a great story. I mean, they have a great comeback story, you know.

SAVIDGE: Wyoming may be the cowboy state. But here, coal is king, but a King Kong scale. Wyoming produces 40 percent of America's coal, dwarfing West Virginia and Kentucky. There's also oil, natural gas, and wind.

MAYOR LOUISE CARTER-KING, GILLETTE, WYOMING: We are the energy capital of the nation.

SAVIDGE: Here, if you're not mining or drilling, you are selling to those who do. This past election, only one issue really matters, jobs and energy. And yes, that's two, but in Wyoming, they are one in the same.

Jeff Dale runs a business renting industrial generators. He voted for Trump saying Democrats were anti-energy.

JEFF DALE, BASIN ELECTRIC POWER: The path that we were on was definitely crippling this industry. So too many regulations and too many hurdles.

SAVIDGE: That could explain why Wyoming was the reddest state of all.

UNIDENTIFIED MALE: 124,000 pounds.

SAVIDGE: Michael (INAUDIBLE) family-owned business has been repairing monster-sized mining machinery for decades. He voted for Trumps and says things have improved ever since.

MIKE WANDLER, L & H INDUSTRIAL INC.: Business is better now. We had the worst year since 2008 last year. It's better now. We feel like it's going to be 100 percent, maybe 20 percent better.

UNIDENTIFIED FEMALE: We're at the table.

SAVIDGE: Stacy (INAUDIBLE) is a sing the parent, a grandma, and a coal miner. She operates at 4100 electric shovel. That's larger than her house. One mistake and you could do a lot of damage.

UNIDENTIFIED FEMALE: Yes, we don't make mistakes.

SAVIDGE: She also voted for Trump and was reviled by his words and actions towards women.

STACY MOOLER, COAL MINER: And I was offended, but it was not about me. It was about the people I work with and the people I love, and I had to make a choice that was bigger than me. So I did.

SAVIDGE: For Stacy and all the voters I talked with, Trump was not a perfect candidate and is not a perfect President. They voted for him believing he would make their lives better. 100 days later, they still do.

Martin Savidge, CNN, Wyoming.

(END VIDEOTAPE)

LEMON: When we come back, I sit down with Caitlyn Jenner and she has some harsh words for the president. Why she says this.

(BEGIN VIDEO CLIP)

JENNER: I would love to go down and play golf with him and say why the hell did you do that?

(END VIDEO CLIP)

(COMMERCIAL BREAK)

[23:37:50] LEMON: It really takes courage to live your life in the spotlight. Your secrets, your heartaches, your mistakes, all of it out there for the world to see. And my next guest is definitely courageous. She is Caitlyn Jenner and her book is out now and it is called "the Secrets of my life."

Caitlyn, welcome. But you say in the book that you don't think you are courageous. Did you?

JENNER: I did say that. It was almost a necessity. I just got to the point in my life where I got that myself. Despite the possibility of tremendous ridicule. I mean, Bruce Jenner, male athlete, American hero, having to deal with this his whole life. And then finally, authentically become myself. And people would look and go, oh my God, this is the weirdest thing I have ever seen. You know, I have risked that, yes. Fortunately, I did have people have been very good.

LEMON: I want to talk to you about it, about the book. By the way, it is welcome. We have been here sitting talking --.

(CROSSTALK)

LEMON: I never thought about the whole time that you have been here, I never thought about Bruce Jenner. Yes, I never thought about it and I grew up with Bruce Jenner. My sister had the biggest crush on you. We watch you.

JENNER: I don't know.

LEMON: But I have paid close attention to you for the last two years. And this book -- I know it's been tough.

JENNER: Yes.

LEMON: Daunting in all of that. You have gotten a lot of criticism, and you have weathered it. What that has been like?

JENNER: Yes. I think a lot of the criticism comes from being more among the conservative Republican side, things that I have said that I didn't word properly. Such as, you know, my support the marriage equality act. This and that, which I do support. I have made mistake for a lot of things over the last two years. But I have tried to learn from those mistakes. I tried to do a better job next time. I learned -- and a lot of the criticism has come from within my community.

LEMON: Do you think it was a mistake to vote for Donald Trump?

JENNER: No. Not yet. Right now. As far as LGBT issues, yes, he has made some mistakes. OK. But other things, I see, we need to turn this country around and he is a guy that I think, for better or worse, I don't support him in everything that he does. But we needed to shake the system up. You know, to have career politicians constantly, the Clintons and, you know, the Bushes run this country, we need to get outside that box and shake things up again.

[23:40:27] LEMON: When he rescinded the Obama air protection for transgender students, you had a message to him. Let's listen.

JENNER: Yes.

(BEGIN VIDEO CLIP)

JENNER: Finally after I message for President Trump, from, well, one Republican to another, this is a disaster. And you can still fix it. You made a promise to protect the LGBTQ community. Call me.

(END VIDEO CLIP)

LEMON: So a lot of people in the LGBT community saw that and felt that what would you expect because he has flip-flopped on a lot. They never thought he was going to protect them.

JENNER: Let me tell you, first of all he brought up it in the inauguration -- or in the convention, the Republican convention. He brought it up. He has been in the past supportive of LGBT issues. There was a girl named Jenna (INAUDIBLE), who was a Trans girl in the Canadian Miss Universe pageant way before all of this in 2012. He supported her right to be able to compete in the Miss Universe pageant, really stood up for the Trans girl. That's a good thing. OK. In other instances he has stood up for the entire LGBT community.

LEMON: He hasn't now, so what do you do? What do you do with --?

JENNER: Watch him really closely. And to be honest with you, the bottom line is, as far as title nine and when that was repealed, I'm going, why do this? There's so many other important issues that the President has to deal with. We have South Korea, we have North Korea, and we have all of these messes. We got to try to build border walls. We have this and that. Why do he even deal with it this? It's not even an issue.

LEMON: OK. Well, let's talk about that a little bit more because I thought it was interesting. And you repeatedly a couple of times, you said that you are -- that you have wealth, that you are entitled, that you're white, you said and you write this, the roles have most definitely switched. You talk about once you were transitioned to Caitlyn. And on the outside, Bruce on the inside, where he will happily remain for the rest of my days.

JENNER: Yes.

LEMON: Bruce will remain on the inside, do you think that you as Bruce are sort of a privileged, you have the mindset of a privileged, older white man and now you're all the sudden --

JENNER: I never -- honestly in my entire life have never felt privileged. I work hard. I didn't start off with everything. I built -- anything I have, I built. I used to live in -- I used to live on $10,000 a year until I was 26 years of age.

LEMON: You don't think it's --

JENNER: $175 car.

LEMON: I understand that, but that's -- a lot of people have strong work ethics.

JENNER: Yes. That was me.

LEMON: But it's harder for a Trans woman who may not be white or who -- it's harder for a black female or a black man or Hispanic man or woman, especially a Trans women to be able to do that.

JENNER: I totally agree with you. And how would you and I team up together and make it better for them? And that's what I'm doing.

LEMON: I would love to do that actually.

JENNER: I would love -- that's my mission. I'm fine. Honestly. I am fine. I have got a roof over my head. I have got wonderful children. I have got a very good life -- I am fine.

LEMON: But, you know, back -- you don't see that as a privilege?

LEMON: JENNER: I want to help that marginalized community. And especially the Trans youth coming up. That's all I do is work on things like that. And so, my loyalties are not with Donald Trump, my loyalties are not with the Republican Party, my loyalties are not with the Democratic Party. My loyalties with my community and I want to make it better and how can we do that.

LEMON: As an LGBT person, I don't think you should put someone in a box. You shouldn't expect an LGBT person to be a democrat or to be liberal. Right?

JENNER: Yes, and we have conservative Republicans like myself, a lot of them.

LEMON: But you said you didn't transition to become a liberal Democrat.

JENNER: Right.

LEMON: Right.

Do you think that sometimes we take those terms, you know, we talk about issues that has to do with the LGBT and maybe it's just some of those issues are not necessarily being a liberal or being a Democrat. It's just being humane or having empathy?

JENNER: No, I agree. I agree that, yes. I agree with that. Because I'm not into really labels either.

LEMON: You said something and I thought -- you said that no question is off-limits, but you think a question that's highly appropriate is about the final surgery for an LGBT person. You admitted that you did. Why did you feel --?

JENNER: Did I say that?

LEMON: Yes, you did.

JENNER: OK.

LEMON: So why did you feel the need share with the world? Because you said it's inappropriate.

JENNER: Because the book is about honesty. And I am -- I tell things in that book that I never thought I would tell anybody in the world about it. You know, and I had to be extremely honest. I talk about a little bit during -- through the book, I draw into reasons to why I came to that decision. That's in the book, but as far as the final surgery, it's really not something that I -- it's extraordinarily personal. It's not something any trance person wants to talk about.

And to be honest with you, most Trans women do not have that surgery done. They are very happy with the way they are. OK. And they don't have it done. Plus it's expensive, it's, you know, tough to do and all that kind of stuff. And so I don't to want disrespect them. Especially if they don't to want go through final surgery, that's fine. You know, just live your life. Doesn't make any difference.

I was no more a woman the day before I had the surgery than I was the day after the surgery. It's just -- the public's perception is they think that that's what it's all about. And it is not about that. It's about my soul. [23:45:54] LEMON: And you're very clear. You said, I am a Trans

woman. I'm not a woman. I can't give birth --

JENNER: I didn't have the same -- my road to womanhood was different than most. Yes.

LEMON: OK. Bridging the gap with conservatives and the LGBT community when we come back.

(COMMERCIAL BREAK)

[23:49:59] LEMON: Caitlyn Jenner is speaking out on LGBT issues in Washington and she is working side by side with CNN political commentator and my friend, Margaret Hoover. And they both join me here.

Margaret, thanks for joining us. So you guys are working together in Washington and write about in the book. Tell me what you guys are doing?

MARGARET HOOVER, CNN POLITICAL COMMENTATOR: Well, I mean, Caitlyn, I couldn't, as a Republican who is advocating for better understanding of LGBT issues could not have fabricated a better silver bullet to walk in and talk to mostly white, mostly older, a lot of men about being transgender. I can't deliver that message but there's no better messenger than Caitlyn Jenner.

JENNER: We have so much fun doing it.

HOOVER: I mean, you should see her in these meetings. Of course, you can't because they are private. But she is extraordinary because she is sharing a really authentic personal experience to people who have never seen a Trans person before.

LEMON: What are they - what are the conversations like? Are they tough conversations?

JENNER: You know what was interesting? One was with a lot of basically evangelical Christians, conservative Republican senators and congressman who had never been anybody who has Trans. But because they knew my story and who I was, they invited me to a very private dinner. And we sat down there and had just great conversation about faith, about religion, about transitioning, about the issues that are out there that, you know, concern Trans people. And it just opened up the conversation to where at the end, one of them in the back says when we get to policy, do you think we can call you? And I'm thinking you might be able to, yes.

LEMON: Have you gotten any calls from the administration?

JENNER: I originally talked to at that time, Trump, on the phone. But no, I haven't gotten. The only -- I have reached out to a senator and we have talked since then on issues and he was absolutely great and that conversation never would have happened if it wasn't for that meeting, that dinner we had.

LEMON: Would you like to meet with the President?

JENNER: Well -- I have. He wants me to play golf with him.

LEMON: We talk about rolling back some of the protections for LGBT.

JENNER: Yes. And that kind of killed it and you saw the video earlier. That thing kind of killed it for me. I can't. I just can't. I would love to, but he wanted to play golf. I would love to go down, even after the fact that he, you know, took this title nine thing away. I would love to go out and play golf with him and say why the hell did you do that? You know, that was like the stupidest thing I have ever seen and tell him that. But now I can't because if I was publicly seen with him, my community would go notch. I would be (INAUDIBLE) from the community. So I would like the have that meeting but I would have it privately and nobody would ever know.

LEMON: Would you think about having it with members of the community? Do you think that he would be open to that?

JENNER: I think he would, yes. If I set it up, yes. I mean, that's - those are things I even had conversation during the inauguration with Mike Pence, you know. As we all know, vice president, when he was, you know, and when he was governor came up with the most anti- LGBT issues and legislation. And so, yes, he needs to talk to. You know, Jeff Sessions needs a talking to but as far as other things, I think I'm not a one issue voter. I mean, there's more to it than just Trans issues.

LEMON: So it is going to take a lot more than just talking, Margaret, as you know.

HOOVER: Look. Here is the thing. I mean, Caitlyn, because she is a Republican, when she goes and talks to Republicans, they believe they are talking to one of them and they are. I mean, she is authentic, right. And so, it's not an organization that has always Republican. It's anti-Republican that hates Republicans going to try to talk about what the issues are facing the Trans community. I mean, she is authentically going in and talking about kids, Trans kids, the suicide rate, the African-American, they hate crimes against Afrcan-American Trans women which are prevalent and rampant in this country.

I mean, she is going to end with all the statistic and really making an authentic case. They can hear it from her in a way they can't hear it from someone else because they that they have a political world view in common. They had an ideology in common. They have a faith in common. And so she has able to cross all these barriers that even I can't cross.

LEMON: But Margaret, you understand if for a Trans-woman, you know, may not have the luxury to vote on other issues, it may just be an one issue voter because it's about life and death and about getting a job for her and they can't understand --

HOOVER: But here is the thing. The reality of our government right now, whether you like it or not and this is what is really difficult for the LGBT community I think sometimes to wrap their head around. You have a Republican President, a Republican Senate, a Republican House of Representatives. That's just at the federal level where we need federal legislation by the way. Then you take all the governors. Two-thirds of the governors are all Republicans. If you're not engaging Republican legislatures, you are not advocating effectively for policy changes that will lead to LGBT freedom in this country.

[23:55:10] LEMON: Yes.

JENNER: I couldn't have said it better.

LEMON: And I couldn't too.

JENNER: Thank you, Margaret.

LEMON: Listen. I have so much to talk about.

JENNER: I know.

LEMON: Would you ever run for office?

JENNER: At first I thought I would never run for office. Why? Because I got way too many secrets. And you know, because I have talked to Republican groups before and they go after your speech and this and that. God, you should run for office. And I have to look -- now I have no more secrets. They are all out. I got nothing, you know. The media couldn't go crazy because they know everything.

LEMON: So answer my darn question.

JENNER: Yes. I would have to look over the next year or two and see can I do a better job on the outside or am I in a position now that I can do a better job for my community on the inside. And if that's the case, if I find it's on the inside, I would seriously look at it. I would seriously look at it.

LEMON: So - and keep your commitment. Be the voice of the voiceless. You have a huge platform. Not that I need to give you any advice. But as long as you do that, I think you will be OK.

JENNER: I just try to keep it real, be myself and keep it real.

LEMON: Thank you.

JENNER: Absolutely.

LEMON: Thank you so much.

JENNER: Thank you.

LEMON: And thank you, Margaret. I will see you soon.

That's it for us tonight. Thanks for watching. I will see you right back here tomorrow.